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WO1998003574A1 - Composes organosilicies fluores et leur procede de preparation - Google Patents

Composes organosilicies fluores et leur procede de preparation Download PDF

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Publication number
WO1998003574A1
WO1998003574A1 PCT/JP1997/002449 JP9702449W WO9803574A1 WO 1998003574 A1 WO1998003574 A1 WO 1998003574A1 JP 9702449 W JP9702449 W JP 9702449W WO 9803574 A1 WO9803574 A1 WO 9803574A1
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WO
WIPO (PCT)
Prior art keywords
formula
group
integer
represented
fluorine
Prior art date
Application number
PCT/JP1997/002449
Other languages
English (en)
Japanese (ja)
Inventor
Yutaka Furukawa
Mami Kotera
Seisaku Kumai
Robert E. Ruckle, Jr.
Gerald J. Murphy
Original Assignee
Asahi Glass Company Ltd.
Osi Specialties, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Asahi Glass Company Ltd., Osi Specialties, Inc. filed Critical Asahi Glass Company Ltd.
Priority to DE69712768T priority Critical patent/DE69712768T2/de
Priority to EP97930797A priority patent/EP0928803B1/fr
Priority to US09/147,542 priority patent/US6197989B1/en
Publication of WO1998003574A1 publication Critical patent/WO1998003574A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention relates to a fluorine-containing organic silicon compound and a method for producing the same.
  • the present invention relates to a novel fluorine-containing organic silicon compound and a method for producing the same. More specifically, the present invention relates to a fluorine-containing organic silicon compound having a hydroxyl group bonded to a Si group via a specific bonding group at both terminals of the molecule, and a method for producing the same.
  • the compound of the present invention is useful as various industrial materials that are required to have performances such as water repellency and oil repellency, antifouling properties, and releasability, and raw materials thereof.
  • Fluorine-containing organic silicon compounds have been applied to various industrial fields due to their lubricity, water / oil repellency, oil resistance / chemical resistance, etc. The above properties are imparted to fats and the like.
  • fluorine-containing organic silicon compounds examples include fluorine-containing silicone oils represented by the following formula 15:
  • x is an integer of 1 or more
  • y is an integer of 0 or more
  • Japanese Patent Application Laid-Open No. H08-92609 discloses a compound directly bonded to at least one terminal silicon atom of a molecule. A fluorine-containing organic silicon compound having a hydroxyl group is shown.
  • the fluorinated organic silicon compound described in Japanese Patent Application Laid-Open No. 8-109260 has a lack in which a hydroxyl group directly bonded to a silicon atom reacts with a hydroxyl group in the air to undergo hydrolysis. There is mosquito.
  • the fluorine-containing organosilicon compound represented by the formula 1 can solve the above problem. Since the compound represented by the following formula 1 has a hydroxyl group formed by bonding to a Si group via a specific bonding group at both ends of the molecule, when added to a resin or the like, the hydroxyl group interacts with the resin. Further, if the resin has a functional group that reacts with a hydroxyl group, the two react with each other, so that the resin can stay in the resin for a long time, and the property of the fluorine-containing organic silicon compound can be maintained for a long time. Over time.
  • the hydroxyl group in the fluorine-containing organic silicon compound is bonded to the Si group via a specific bonding group, there is no risk that the hydroxyl group is hydrolyzed, and there is an advantage that the stability of the compound is high. .
  • a fluorine-containing organic silicon compound represented by the following formula 1 is provided.
  • a f is one or more selected from monovalent polyfluorohydrocarbon group-containing organic groups represented by Formulas 2, 3, and 4 (wherein, in Formulas 2 to 4, A 1 A represents a monovalent polyfluorohydrocarbon group; A 2 represents a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom; A 3 represents a monovalent polyfluorohydrocarbon group; X ′, X 2 , ⁇ : ', X 4 and chi' 5 each independently represents a divalent hydrocarbon group.
  • R ′ and R 2 each independently represent a divalent organic group; R 3 to R 9 each independently represent a divalent organic group; a is an integer of 1 or more; b is 0 or more It is an integer.
  • the H-Si group-containing organic silicon compound represented by the following formula 8 is selected from the fluorine-containing unsaturated compounds represented by the following formulas 9, 10 and 11:
  • a method for producing a fluorine-containing organosilicon compound, comprising adding at least one kind, is provided.
  • R : 'to R 9 a and b are the same as defined in Formula 1; r, s, and i each independently represent an integer of 07.
  • a fluorine-containing cyclic compound represented by the following formula 13 is optionally replaced with a carbonized compound represented by the following formula 14 in the presence of the compound represented by the following formula 12:
  • a method for producing a fluorine-containing organic silicon organic compound represented by the formula (1) which comprises ring-opening polymerization together with a hydrogen-based cyclic body.
  • the fluorine-containing organic silicon compound of the present invention is represented by the following formula (1).
  • R 1 and R each independently represent a divalent organic group
  • R : 1 to R 9 each independently represent a monovalent organic group.
  • the “organic group” is a group containing carbon, and is preferably a hydrocarbon group.
  • the “hydrocarbon group” in the present specification refers to a group consisting of a carbon atom and a hydrogen atom unless otherwise specified.
  • the hydrocarbon group any of an aromatic hydrocarbon group and an aliphatic hydrocarbon group can be used, but an aliphatic hydrocarbon group is preferable, and an alkyl group is particularly preferable.
  • RR 9 is preferably a monovalent hydrocarbon group, particularly preferably an alkyl group.
  • RR 2 is preferably a divalent hydrocarbon group, particularly preferably an alkylene group.
  • the alkyl group and the alkylene group preferably have about 1 to 10 carbon atoms, particularly preferably 1 to 4 carbon atoms.
  • Each of the alkyl group and the alkylene group preferably has a linear structure.
  • a f represents one or more selected from the polyfluorocarbon group-containing organic groups represented by the following formulas 2, 3 and 4, and one is preferred.
  • a ′ and A J each independently represent a monovalent polyfluorohydrocarbon group, and A ; represents a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom.
  • Polyfluorohydrocarbon group refers to a group in which two or more hydrogen atoms of a hydrocarbon group have been substituted with fluorine atoms, and a polyfluoroalkyl group is preferred.
  • polyfluorohydrocarbon group containing an etheric oxygen atom refers to a group in which an etheric oxygen atom is inserted between the carbon-carbon bonds of the above-mentioned polyfluorohydrocarbon group. Groups containing an alkylene moiety are preferred.
  • the number of fluorine atoms in the polyfluorohydrocarbon group is (number of fluorine atoms in the polyfluorohydrocarbon group) no (number of hydrogen atoms in the hydrocarbon group having the same number of carbon atoms corresponding to the polyfluorohydrocarbon group)
  • XI 00 (% ) Is preferably 60% or more, particularly preferably 80% or more, and more preferably substantially 100%, that is, substantially all of the hydrogen atoms of the hydrocarbon group are fluorine atoms. It is preferable that the group is a group substituted by ("a perfluorohydrocarbon group").
  • polyfluorohydrocarbon groups may have a straight-chain or branched structure, but a straight-chain structure is particularly preferable.
  • the branched portion is preferably a short chain having about 1 to 3 carbon atoms, and is preferably a structure existing at the terminal of A 1 and A 8 : 1 .
  • a ′ and A 3 are preferably a polyfluoroalkyl group, and more preferably a perfluoroalkyl group. Specific examples include the following examples. In addition, in the following specific examples, groups corresponding to the respective groups of structural isomerism are also included.
  • a 2 is preferably a group containing a polyfluorooxyalkylene moiety, particularly preferably a group containing a monofluorooxyalkylene moiety. Further, A 2 is preferably a group containing a perfluoroalkylene moiety and having a terminal perfluoroalkyl group. Examples of the perfluorooxyalkylene include perfluoro-xylene, xylene, perfluoro-xylene, norphoxylate-propylene, perfluorooxybutylene and the like.
  • a 2 groups include those exemplified below. In the following specific examples, groups corresponding to respective structurally isomer groups are also included.
  • X ′, X 2 , X 3 , X 4 and X 5 each independently represent a divalent hydrocarbon group.
  • the divalent hydrocarbon group is preferably an alkylene group, and may have a linear or branched structure. However, in the present invention, — (CH 2 ) p — (where p is 1 to 1) An integer of 0, preferably an integer of 2 to 4) is preferable. In the case of a branched structure, those having a short chain having about 3 to 3 carbon atoms in the branched portion are preferred.
  • the above formula 2 is preferably represented by the following formula 5.
  • n is an integer of 4 to 18, preferably 6 to 2; X 'is as defined above; and a linear alkylene group is preferable.
  • the above formula 3 is preferably represented by the following formula 6.
  • m is an integer of 1 to 10, preferably 1 to 5, and X 2 and X : ⁇ are each as defined above, and are preferably a linear or linear alkylene group. .
  • the above formula 4 is preferably represented by the following formula 7.
  • k is an integer of 1 to 18 and preferably an integer of 4 to 12
  • X 1 and X 5 are each as defined above.
  • a is an integer of 1 or more, preferably from 5 to 50 (), particularly preferably from 5 to 30.
  • b is an integer of 0 or more, preferably 5 to 1 () () 0, and particularly preferably 25 to 40.
  • aZb can be appropriately changed depending on the fluorine content, but is preferably 1Z0.5 to lZ9, and particularly preferably 1Z:! to 1/3.
  • 10 ⁇ (a + b) ⁇ 70 is preferable, and particularly, 20 ⁇ (a + b) ⁇ 40 is preferable.
  • the fluorine-containing organic Kei-containing compound represented by the formula 1 of the present invention for preferably Ru Oh an oil at ordinary temperature, the molecular weight] X 1 0: i ⁇ ] X 1 0 about 6, more preferably Is 5 ⁇ 10: ′ ⁇ 15 ⁇ 10 3 .
  • the fluorine content in the fluorine-containing organic silicon compound represented by the formula 1 is preferably 15 to 90% by weight, more preferably 15 to 70% by weight.
  • fluorine-containing organic silicon compound of the formula 1 of the present invention includes both cases of a block polymer and a random polymer. The same applies to other compounds.
  • fluorinated organic silicon compound represented by the formula 1 of the present invention include the following, but are not limited thereto.
  • Examples including a group represented by Formula 2 (a is an integer of 1 or more, preferably an integer of 10 to 50; b is an integer of 0 or more, and an integer of 20 to 6 () is preferable. ):
  • Examples including a group represented by Formula 3 (a is an integer of 1 or more, and an integer of 10 to 50 B is an integer of 0 or more, preferably an integer of 20 to 60. ): H0 (Hi l 2 ) 3 Si (CH :,) 20 ⁇ ⁇ Si (Cll) [(C3 ⁇ 4) 0CH 2 CF (CF : 1 ) (OCF, CFCF.,), F] 0 ⁇ paragraph ⁇
  • the fluorinated organosilicon compound of the present invention comprises at least one monovalent polyfluorohydrocarbon group selected from the above formulas 2 to 4, and preferably at least one monovalent polyfluorocarbon group selected from the formulas 5 to 7.
  • a hydrogen group is bonded to a silicon atom.
  • the fluorine-containing organic silicon compound represented by the above formula 1 of the present invention can be synthesized mainly by the following two synthesis methods. That is, at least one of the fluorine-containing unsaturated compounds represented by the formulas 9 to 11 is added to the H-Si group-containing organic silicon compound represented by the formula 8 as a transition metal catalyst.
  • an H-Si group-containing organic silicon compound represented by the following formula 8 (hereinafter referred to as “hydrosilicone compound”) is added to the following formulas 9, 10 and 11: by adding at least one member selected from among fluorine-containing unsaturated compounds, X ', X:', X 5 gar (CHJ q - (wherein, q is an integer from 3 1 0 )), The fluorine-containing organic silicon compound represented by the formula 1 is produced.
  • each substituent in Formulas 8 to 10 has the same meaning as the definition of each substituent described in Formulas 1 to 7 above, and r, s, and t each represent an integer of 0 to 7. . r, s, and t are each preferably 0.
  • the fluorinated unsaturated compound of the formulas 9 to 1 can be added to the H—Si portion of the compound represented by the formula 8.
  • the compounds of the formulas 9 to 11 one or more compounds can be used.
  • a ′, A 2 and A : ′ are groups having different numbers of carbon atoms.
  • the hydrosilylation may be performed in the presence of a solvent or substantially without a solvent, and is preferably performed without a solvent.
  • the amount of the solvent contained in the reaction system is preferably 0 (not contained at all), but the amount of the solvent used for preparing the reagent used in the reaction, for example, the solvent for dissolving the catalyst If the amount is as small as possible, there is no problem.
  • the amount of the solvent in the reaction system is preferably about 1% by weight or less, and more preferably 0 to 0.1% by weight or less.
  • the hydrosilation is in the presence of a catalyst.
  • a catalyst containing a transition metal is preferable, and a catalyst containing platinum, rhodium, and cobalt is particularly preferable.
  • the reaction temperature is usually preferably about 70 to 100.
  • the reaction time can be appropriately changed depending on the compound to be used, and is usually about 0.5 to 10 hours. In the case of the present invention, the reaction can proceed even for a short time. 5 hours is preferred.
  • the amount of the catalyst is usually about 1 to 10 ppm in the reaction system. However, in the present invention, even when the amount of the catalyst is reduced, the reaction can proceed in a short time, so that the amount is about 0.0 to 10 ppm. preferable.
  • the amount of the fluorinated unsaturated compound represented by Formulas 9 to 11 in the hydrosilylation is based on one equivalent of the hydrogen atom bonded to the silicon atom in the hydrosilicone compound represented by Formula 8. , 1 equivalent or more, more preferably 1.1 to 2 equivalents.
  • the compound represented by Formula 1 produced by the synthesis method 1 has no risk of containing volatile cyclic siloxane derived from raw materials and by-products, and the compound produced without using a solvent has an adverse effect due to residual solvent. It is particularly preferable because there is no need to worry about
  • the fluorine-containing organic silicon compound represented by the formula 1 of the present invention can also be synthesized by a ring-opening polymerization method (synthesis method 2).
  • synthesis method 2 a fluorine-containing cyclic trisiloxane represented by the following formula 13 and, if necessary, a cyclic polysiloxane represented by the following formula 14 are opened in the presence of the compound represented by the following formula 12: It can be synthesized by ring polymerization.
  • AR 3 to R 9 have the same meaning as described above, c represents an integer of 3 or more, and 4 is preferable.
  • the amounts of the formulas 13 and 14 with respect to the compound represented by the formula 12 are appropriately changed depending on the structure of the compound represented by the formula 1 which is the target compound.
  • the compound represented by the formula] 3 is added to the (a + b) Zl ()-(a + b) / 150 It is preferable to use a mole, and in particular, it is preferable to use (a + b) Z 40-(a + b) / ⁇ 0 mole (a and b have the same meanings as a and b in Formula 1).
  • a polymerization catalyst known acid catalysts and alkali catalysts used for ring-opening polymerization are arbitrarily used. Sulfuric acid and trifluoromethanesulfonic acid are preferred as the acid catalyst.
  • alkali catalyst examples include alkali metal hydroxides such as sodium hydroxide, lithium hydroxide, and potassium hydroxide.
  • These catalysts are neutralized after ring-opening polymerization and removed by filtration or the like. This neutralization can be performed by adding a basic substance when an acidic catalyst is used, and by adding an acidic compound when an alkaline catalyst is used.
  • the amount of the polymerization catalyst is ⁇ 100 ppm based on the total weight of the compound represented by the formula 12, the compound represented by the formula 13, and optionally the compound represented by the formula 14. Is particularly preferable, and 1 to 100 ppm is particularly preferable.
  • the polymerization temperature is preferably from 20 to 200 ° C, more preferably from 40 to ⁇ 50 ° C.
  • the polymerization time is preferably 0.5 to 10 hours.
  • X, X 3 and X 5 in the formula 1 are each —CH 2 — or 1 CH 2 CH 2 — preferably a compound, in particular compound of one CH 2 CH 2 are preferred.
  • the use of the fluorinated silicone compound of the present invention is not particularly limited. However, by adding it to a functional oil, a resin, a rubber, or the like, the surface tension or the refractive index can be reduced, and the electrical insulation, the releasability, and the repellency can be reduced. Aqueous, defoaming, oil resistance, solvent resistance, lubricity and heat resistance can be provided.
  • a resin having a group reactive with the terminal hydroxyl group of the fluorine-containing silicone compound is selected, there is an advantage that the effect of preventing the fluorine-containing silicone compound from bridging out of the resin becomes higher. .
  • the fluorine-containing silicon compound of the present invention has an advantage that the use environment and storage conditions are not limited because terminal hydroxyl groups are not likely to be partially hydrolyzed and condensed even when moisture is present in the air. is there.
  • the fluorine-containing organosilicon compound represented by the formula 1 of the present invention can be used for various anti-fouling oils for copy rolls, various lubricating oils such as refrigerating machine oil and vacuum pump oil, truncation oil, brake oil, coupling Various hydraulic oils and other hydraulic oils, instruments for automobiles and aircraft, anti-vibration oils for player pickups, damper oils such as dashpots and shock absorbers, thermal transfer recording receivers, magnetic recording media, magnetic heads, Lubricants for impregnated bearings, release agents, release agents, roll compositions for copiers and printers or their surface coating agents, compounding agents for shampoo, rinse, various makeup cosmetics, and various powder treatment agents , Water and oil repellents, deep color processing agents, lubricating agents for textiles, insulating oils such as transformer oils, condenser oils, cable oils, leveling agents, anti-blocking agents, color unevenness preventing agents Yuzu Additive to polymer materials in plastics and paints as a skin inhibitor etc., rubber ⁇
  • the coating film was left for 6 months, and a line was similarly drawn with an oil-based felt pen (black). After 5 minutes, the film was wiped off with a paper pallet. As a result, no trace was left.
  • a coating film was similarly formed without adding the compound represented by the formula 24 in Example 5.
  • a line was drawn on the surface of the coating film with an oil-based felt pen (black), and after 5 minutes, wiped off with paper.
  • the fluorine-containing organic silicon compound of the present invention can be added to a functional oil, a resin, a rubber, or the like to lower the surface tension or the refractive index, to provide electrical insulation, release properties, water repellency, and defoaming properties. It can provide oil, oil, solvent, lubricity, and heat resistance, and is useful as a raw material for various industrial materials that require performance such as water / oil repellency, antifouling properties, and mold release properties. It is.
  • the fluorine-containing organic silicon compound of the present invention has a hydroxyl group formed by bonding to a Si group via a specific bonding group at both ends of the molecule. It is possible to continuously impart the properties of That is, when adding to a resin, if the resin has a group reactive with the terminal hydroxyl group of the fluorinated silicone compound, there is an advantage that the fluorinated silicone compound can be prevented from bleeding out of the resin. .
  • fluorine-containing silicone compounds synthesized by hydrosilylation are advantageous in preventing bleed-out from resin because there is no possibility that unreacted low-molecular compounds remain.
  • the fluorine-containing silicone compound of the present invention is advantageous in that the use environment and storage conditions are not limited even if water is present in the air, since there is no possibility that the terminal hydroxyl groups are partially hydrolyzed and condensed. There is also.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)

Abstract

Composés organosiliciés fluorés de la formule générale (1), destinés à être utilisés comme matériaux hydrofuges et oléofuges ainsi que comme divers autres matériaux industriels qui doivent présenter des caractéristiques de résistance aux taches, d'anti-adhérence et autres, ou comme matières brutes pour ces derniers. Dans la formule générale (1), Af est un groupe organique spécifique contenant un groupe polyfluorohydrocarboné; R1 et R2 sont chacun indépendamment un groupe organique divalent; R3 à R9 sont chacun indépendamment un groupe organique monovalent; a est un entier valant au moins 1; et b est un entier valant au moins 0.
PCT/JP1997/002449 1996-07-18 1997-07-15 Composes organosilicies fluores et leur procede de preparation WO1998003574A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE69712768T DE69712768T2 (de) 1996-07-18 1997-07-15 Fluorierte organosiliconverbindungen und verfahren zu ihrer herstellung
EP97930797A EP0928803B1 (fr) 1996-07-18 1997-07-15 Composes organosilicies fluores et leur procede de preparation
US09/147,542 US6197989B1 (en) 1996-07-18 1997-07-15 Fluorinated organosilicon compounds and process for the preparation thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/207776 1996-07-18
JP20777696 1996-07-18

Publications (1)

Publication Number Publication Date
WO1998003574A1 true WO1998003574A1 (fr) 1998-01-29

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PCT/JP1997/002449 WO1998003574A1 (fr) 1996-07-18 1997-07-15 Composes organosilicies fluores et leur procede de preparation

Country Status (4)

Country Link
US (1) US6197989B1 (fr)
EP (1) EP0928803B1 (fr)
DE (1) DE69712768T2 (fr)
WO (1) WO1998003574A1 (fr)

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EP0928803A1 (fr) 1999-07-14
EP0928803B1 (fr) 2002-05-22
DE69712768D1 (de) 2002-06-27
DE69712768T2 (de) 2003-01-23
US6197989B1 (en) 2001-03-06

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